M1G-dR

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531402

CAS#: 87171-83-3

Description: M1G-dR, also known as 3-(2'-Deoxyribofuranosyl)pyrimido(1,2-a)purin-10(3H)-one, is a malondialdehyde-deoxyguanosine adduct. M1G-dR is a major DNA adduct produced by lipid peroxidation. Furthermore, the number of double bonds in polyunsaturated fatty acids was found to be the key factor in the formation of M1G-dR. The findings obtained from this study provide important information regarding the molecular pathways for M1G-dR formation by ROS, which is an essential element in understanding and evaluating the genotoxicity of a variety of ROS-inducing chemicals.


Chemical Structure

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M1G-dR
CAS# 87171-83-3

Theoretical Analysis

MedKoo Cat#: 531402
Name: M1G-dR
CAS#: 87171-83-3
Chemical Formula: C13H13N5O4
Exact Mass: 303.0968
Molecular Weight: 303.278
Elemental Analysis: C, 51.49; H, 4.32; N, 23.09; O, 21.10

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: M(1)G-deoxyribose; M1G-dR;

IUPAC/Chemical Name: 3-(2'-Deoxyribofuranosyl)pyrimido(1,2-a)purin-10(3H)-one

InChi Key: QZDHOBJINVXQCJ-ZQTLJVIJSA-N

InChi Code: InChI=1S/C13H13N5O4/c19-5-8-7(20)4-9(22-8)18-6-15-10-11(18)16-13-14-2-1-3-17(13)12(10)21/h1-3,6-9,19-20H,4-5H2/t7-,8+,9?/m0/s1

SMILES Code: O=C1N2C(N=CC=C2)=NC3=C1N=CN3C4C[C@@H]([C@@H](CO)O4)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 303.278 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Moore SA, Xeniou O, Zeng ZT, Humphreys E, Burr S, Gottschalg E, Bingham SA, Shuker DE. Optimizing immunoslot blot assays and application to low DNA adduct levels using an amplification approach. Anal Biochem. 2010 Aug;403(1-2):67-73. doi: 10.1016/j.ab.2010.04.015. Epub 2010 May 14. PMID: 20399191.

2: Schnetz-Boutaud NC, Chapeau MC, Marnett LJ. Enzymatic synthesis of M(1)G-deoxyribose. Curr Protoc Nucleic Acid Chem. 2001 May;Chapter 1:Unit1.2. doi: 10.1002/0471142700.nc0102s00. PMID: 18428817.

3: Jeong YC, Swenberg JA. Formation of M1G-dR from endogenous and exogenous ROS- inducing chemicals. Free Radic Biol Med. 2005 Oct 15;39(8):1021-9. doi: 10.1016/j.freeradbiomed.2005.05.018. PMID: 16198229.

4: VanderVeen LA, Druckova A, Riggins JN, Sorrells JL, Guengerich FP, Marnett LJ. Differential DNA recognition and cleavage by EcoRI dependent on the dynamic equilibrium between the two forms of the malondialdehyde-deoxyguanosine adduct. Biochemistry. 2005 Apr 5;44(13):5024-33. doi: 10.1021/bi0472898. PMID: 15794640.

5: Jeong YC, Sangaiah R, Nakamura J, Pachkowski BF, Ranasinghe A, Gold A, Ball LM, Swenberg JA. Analysis of M1G-dR in DNA by aldehyde reactive probe labeling and liquid chromatography tandem mass spectrometry. Chem Res Toxicol. 2005 Jan;18(1):51-60. doi: 10.1021/tx049853l. PMID: 15651849.

6: Riggins JN, Pratt DA, Voehler M, Daniels JS, Marnett LJ. Kinetics and mechanism of the general-acid-catalyzed ring-closure of the malondialdehyde-DNA adduct, N2-(3-oxo-1-propenyl)deoxyguanosine (N2OPdG-), to 3-(2'-Deoxy-beta-D- erythro-pentofuranosyl)pyrimido[1,2-alpha]purin- 10(3H)-one (M1dG). J Am Chem Soc. 2004 Sep 1;126(34):10571-81. doi: 10.1021/ja040010q. PMID: 15327313.

7: Hong CC, Tang BK, Rao V, Agarwal S, Martin L, Tritchler D, Yaffe M, Boyd NF. Cytochrome P450 1A2 (CYP1A2) activity, mammographic density, and oxidative stress: a cross-sectional study. Breast Cancer Res. 2004;6(4):R338-51. doi: 10.1186/bcr797. Epub 2004 May 7. PMID: 15217501; PMCID: PMC468635.

8: Hoberg AM, Otteneder M, Marnett LJ, Poulsen HE. Measurement of the malondialdehyde-2'-deoxyguanosine adduct in human urine by immuno-extraction and liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry. J Mass Spectrom. 2004 Jan;39(1):38-42. doi: 10.1002/jms.547. PMID: 14760611.

9: Otteneder M, Plastaras JP, Marnett LJ. Reaction of malondialdehyde-DNA adducts with hydrazines-development of a facile assay for quantification of malondialdehyde equivalents in DNA. Chem Res Toxicol. 2002 Mar;15(3):312-8. doi: 10.1021/tx010105v. PMID: 11896677.

10: Leuratti C, Watson MA, Deag EJ, Welch A, Singh R, Gottschalg E, Marnett LJ, Atkin W, Day NE, Shuker DE, Bingham SA. Detection of malondialdehyde DNA adducts in human colorectal mucosa: relationship with diet and the presence of adenomas. Cancer Epidemiol Biomarkers Prev. 2002 Mar;11(3):267-73. PMID: 11895876.

11: Schnetz-Boutaud NC, Saleh S, Marnett LJ, Stone MP. Structure of the malondialdehyde deoxyguanosine adduct M1G when placed opposite a two-base deletion in the (CpG)3 frameshift hotspot of the Salmonella typhimurium hisD3052 gene. Adv Exp Med Biol. 2001;500:513-6. doi: 10.1007/978-1-4615-0667-6_77. PMID: 11764989.

12: Schnetz-Boutaud NC, Saleh S, Marnett LJ, Stone MP. The exocyclic 1,N2-deoxyguanosine pyrimidopurinone M1G is a chemically stable DNA adduct when placed opposite a two-base deletion in the (CpG)3 frameshift hotspot of the Salmonella typhimurium hisD3052 gene. Biochemistry. 2001 Dec 25;40(51):15638-49. doi: 10.1021/bi011242u. PMID: 11747439.

13: Lee SH, Blair IA. Oxidative DNA damage and cardiovascular disease. Trends Cardiovasc Med. 2001 Apr-May;11(3-4):148-55. doi: 10.1016/s1050-1738(01)00094-9. PMID: 11686005.

14: Everett SM, Singh R, Leuratti C, White KL, Neville P, Greenwood D, Marnett LJ, Schorah CJ, Forman D, Shuker D, Axon AT. Levels of malondialdehyde- deoxyguanosine in the gastric mucosa: relationship with lipid peroxidation, ascorbic acid, and Helicobacter pylori. Cancer Epidemiol Biomarkers Prev. 2001 Apr;10(4):369-76. PMID: 11319178.

15: Leuratti C, Singh R, Deag EJ, Griech E, Hughes R, Bingham SA, Plastaras JP, Marnett LJ, Shuker DE. A sensitive immunoslot-blot assay for detection of malondialdehyde-deoxyguanosine in human DNA. IARC Sci Publ. 1999;(150):197-203. PMID: 10626221.

16: Ji C, Rouzer CA, Marnett LJ, Pietenpol JA. Induction of cell cycle arrest by the endogenous product of lipid peroxidation, malondialdehyde. Carcinogenesis. 1998 Jul;19(7):1275-83. doi: 10.1093/carcin/19.7.1275. PMID: 9683189.

17: Niedernhofer LJ, Riley M, Schnetz-Boutaud N, Sanduwaran G, Chaudhary AK, Reddy GR, Marnett LJ. Temperature-dependent formation of a conjugate between tris(hydroxymethyl)aminomethane buffer and the malondialdehyde-DNA adduct pyrimidopurinone. Chem Res Toxicol. 1997 May;10(5):556-61. doi: 10.1021/tx960191c. PMID: 9168253.

18: Rouzer CA, Chaudhary AK, Nokubo M, Ferguson DM, Reddy GR, Blair IA, Marnett LJ. Analysis of the malondialdehyde-2'-deoxyguanosine adduct pyrimidopurinone in human leukocyte DNA by gas chromatography/electron capture/negative chemical ionization/mass spectrometry. Chem Res Toxicol. 1997 Feb;10(2):181-8. doi: 10.1021/tx9601216. PMID: 9049429.

19: Sevilla CL, Mahle NH, Eliezer N, Uzieblo A, O'Hara SM, Nokubo M, Miller R, Rouzer CA, Marnett LJ. Development of monoclonal antibodies to the malondialdehyde-deoxyguanosine adduct, pyrimidopurinone. Chem Res Toxicol. 1997 Feb;10(2):172-80. doi: 10.1021/tx960120d. PMID: 9049428.

20: Chaudhary AK, Reddy GR, Blair IA, Marnett LJ. Characterization of an N6-oxopropenyl-2'-deoxyadenosine adduct in malondialdehyde-modified DNA using liquid chromatography/electrospray ionization tandem mass spectrometry. Carcinogenesis. 1996 May;17(5):1167-70. doi: 10.1093/carcin/17.5.1167. PMID: 8640930.